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Styling Tips: How to Dress When Losing Weight

When you’re focused on losing weight, leaning out or changing body composition, you might not want to spend money on clothes (or you think you don’t). Or maybe you see a lot of change and realize you need a whole new wardrobe.

What I’ve seen with clients who have gone through a weight loss transformation or body composition change, is that they don’t really know how to dress themselves anymore. What’s hard about this kind of change, is that your mind doesn’t catch up with the changes in your body. So you may see yourself as a larger size than you actually are. 

During this time of change, if you’ve never experienced a personal styling service, or if you have, but you’ve never tried Trunk Club – I recommend people try it. Trunk Club is a major sponsor of the 60-Day Challenge, and is congratulating anyone who crossed the finish line and weighed out with us with $60 off his or her trunk.

I personally had an awful experience with another personal styling service, so I was excited about Trunk Club because I had heard really great things about it. I decided to give it a go and wanted to share my experience with you.


What I enjoyed most about Trunk Club was the personalization. Unlike other companies, the stylist actually calls you on the phone and asks you questions like, “What colors do you like?” and “What do you like to wear?” Once they get to know you, your journey and how you’re trying to dress — they do all the hard work for you. They not only shop for you based off of the styles and color palate you like, but they’ll also include their own picks as professional stylist. Then they’ll send a sneak peek of what they’ve chosen before you receive it (so you can say no to any of the choices and they’ll even re-shop for you). I decided to accept everything my personal stylist suggested. Although I think I know what I like to wear, and saw a few things in my cart I thought I’d never like, I decided to roll with it. 

This is the best part, they send you a beautifully wrapped package with all of your personally curated clothing choices. They encourage you to try everything on, so once it arrives — make sure to try on each and every piece so you can have the full experience.

My problem? I liked everything. Each and every item was perfect and in the right color palates. There were also really unique pieces that I loved. The clothing that I chose to keep were items that I would never have picked out for myself which was fun. I also liked the variety they sent. I mentioned I was a part of a weight loss challenge in our initial conversation, so they sent a lot of cardigans, which I appreciated. Because if the goal is weight loss, you want solid pieces you can wear throughout different stages of your weight loss journey. They also included really cute dark pants which are really easy to transition from work until night, which is really important for me. I work a lot and I’m a mom so I want to be comfortable all-day long. I loved that my stylist could send me clothes for any occasion in my life — whether I’m chasing my kids around, going on a date with my partner, or going to the gym for a workout. They even have cute activewear that I can wear at Life Time. 

There’s also no obligation with Trunk Club. You get to decide what you want to keep and then just return the clothes you don’t want in the box they include. They even include a pre-paid shipping label to help you send it back and can help you arrange a UPS pickup, so the returns process is easy. And whatever you do like and want to keep — you can use the $60 credit towards and pay the remainder with your credit card. You can schedule trunks monthly, quarterly or whatever works for you. Plus, I really appreciated how easy it was to exchange an item for another size or color and to give feedback.

Takeaway? I truly enjoyed my Trunk Club experience and I’ll definitely do it again in the spring. I loved that I could try everything on in the comfort of my own home, that it’s personalized, super convenient and time-saving. Getting a package was so much fun, and everything was so beautifully folded — I felt like I was opening a gift. Trunk Club is not only convenient, but they provide expert styling advice (we can all use experts in different areas of our lives), which comes in handy when you’re transforming your body.

In my experience, I really think one of the worst things you can do when losing weight and transforming your body is to wear things that are too big. Finding really great staples that make you look and feel good is so important in a journey like this.

Many of my clients are fearful to purchase new clothes as they continue to lose weight, thinking that they’ll simply end up wasting money with a succession of clothes that don’t fit. The way I see it, however, is that every client of mine deserves to look his/her best and have clothes that show it along the course of the journey itself. 

My motto for my clients is to never sacrifice their appearance during their weight loss journey. And to continually practice positive self-care to help them stay on the path — and to look and feel their best. With that in mind, here are 5 tips for making the most of in-transition purchases and strategizing your look for the long-term.


Believe me, I know it feels good to wear clothes that are too big for you that were previously snug. I distinctly remember this feeling when I significantly changed my body composition and my jeans and pants were literally almost falling off of me. Wearing them made me feel good and served as a great reminder of what I had accomplished, but I looked ridiculous. The fact is, you want to avoid wearing clothes that hide your shrinking body. Go through your closet piece by piece and pitch or donate any clothes that don’t fit you properly anymore as well as anything else that is too old or out of style.


Although we may love the idea of getting into a size 4 jean, focusing on the number first tends to get us in trouble. Take the power of that number away and go for clothes (in whatever size) that look and feel good.

You may be able to fit into one size but look worlds different and even better in another size. And it’s not always easy to gage our size after losing weight or changing shape. I loved that my Trunk Club stylist helped me to identify my proper size in each brand. 


“I could never pull off an outfit like that,” or “I don’t have the right body shape for a dress like that,” are common comments I hear from my clients. When they transform their bodies, one of my favorite challenges to give them is to buy — or at very least try on — an outfit that they would have never pictured themselves wearing before. My stylist sent me options that I never thought I would like, but in the spirit of trying something new I kept them in my Trunk and am happy that I did. It’s fun to try something new, but oftentimes it gets people to see that clothes they’ve avoided genuinely look good on them. It can be the ultimate confidence boost to see yourself in a whole new light!

Also, take note of styles or articles of clothing that your friends or coworkers wear that you like to get some ideas for yourself, and make a point to buy one of these pieces at every weight loss milestone.  You can even show this inspiration to your stylist and she can help put together similar looks that work perfectly with your changing body composition. 


Investing in accessories, such as belts, can be great when you’re in between sizes or not ready to purchase the next size smaller pants. Belts can accentuate your new waistline and be a great tool to show how you’re progressing toward your goal as you make your way through the notches on the belt. 

Other accessories, such as scarves, jewelry, etc., are also great ways to create new looks that aren’t size specific. 


Maybe it’s for shopping support or going through your existing wardrobe. The fact is, a close friend or relative can give you a second opinion on whether something fits or looks good. Because it can take time for our mindsets to catch up to our physical transformations, you may still have a certain image in your head of what you look like. I also love the idea of using a Trunk Club stylist as another opinion, especially because they didn’t know you before your weight loss journey, and can give you some fresh styling ideas based off your current size. They can also push you toward taking a risk on new and flattering styles you wouldn’t automatically choose for yourself.


In health, Anika Christ – Director – Digital Programming & Events – Life Time Weight Loss 

This article is not intended for the treatment or prevention of disease, nor as a substitute for medical treatment, nor as an alternative to medical advice. Use of recommendations in this and other articles is at the choice and risk of the reader.

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